


It's Very Complex

by GlitterDwarf



Category: Supernatural
Genre: AU: High school and college, M/M, Spanking
Language: English
Status: Completed
Published: 2013-02-03
Updated: 2013-02-03
Packaged: 2017-11-28 02:44:19
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,213
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/669338
Author URL: https://archiveofourown.org/users/GlitterDwarf/pseuds/GlitterDwarf
Summary: <blockquote class="userstuff">
              <p>Cas has been spending too much time babysitting and not enough time paying attention to Dean. This is, of course, a punishable offense, and who better to punish a babysitter than a pizza man? College/High School AU. (Filling a prompt.)</p>
            </blockquote>





	It's Very Complex

**Author's Note:**

> Done for this prompt from destielficprompts.tumblr.com:
> 
> "Dean is the pizza man, Cas it the babysitter. maybe this has been done before, but i haven’t seen it! perhaps this is the chance for two young guys who’ve been making eyes at each other for years to finally give it a whirl, or maybe its the opportunity for one very bored babysitter and one very underpaid pizza man to make a night of things… "
> 
> This got a lot more elaborate and schmoopy and way out of control. This was going to be short originally. And then...

Then, there was an awkward pause. Dean coughed and shifted his cell from one ear to the other, which gave him room to reach into the cabinet for the small serving plate.   
  
“I didn’t think it was a weird question, Cas,” Dean mumbled as he set the plate down. It sounded loudly, too-loudly in the small kitchen. “Or are you too busy with your new life in college to hang out with me on Fridays anymore?”  
  
“No, it’s not that,” Cas answered over the phone. His voice was slow and gravely. Dean forced back a shudder; hearing that voice so close to his ear was just _not fair_. “I have a...job."

  
Cas trailed off. Dean served himself a healthy portion of apple pie and stuffed a substantial piece in his mouth.   
  
“What job?”  
  
“Dean, please don’t speak to me with your mouth full. And if you have to know, I’m babysitting.”  
  
An image flashed through Dean’s mind of Cas the babysitter in a short skirt, knee-high socks and shiny lips, bent over to be punished by the father for breaking into the liquor cabinet. Dean swallowed, hard.  
  
“Kinky.”

  
“What was that?”  
  
“A joke,” Dean said quickly. He coughed self-consciously to fill up the silence before his brain caught up with his mouth. “Why are you babysitting, Cas? You already have a job.”  
  
“I’m saving up. I’ll be babysitting on Fridays for a while.”  
  
“But what about me?”  
  
“Dean, it isn’t like we’ll never see each other.”  
  
Another pause. Dean took the opportunity to stuff more pie in his mouth, but for some reason he couldn’t fully enjoy it.  
  
\---  
  
Dean started on Facebook, where every day for a week he posted a tally of the number of days that he hadn’t seen Cas, adding a joke at the end of every status. It was on day eight when he stopped posting this in public; after all, there were only so many days where a guy could publically complain about not seeing his best friend before things started looking a little weird.  
  
After this, he started texting Castiel directly instead. At first the responses were jokes, light teasing before they continued their normal text conversations. However, Castiel's responses started coming later apart and fewer. Eventually his responses were quick apologies, and their phone calls were always cut short by Castiel falling asleep over the phone, no matter what time of day Dean called.   
  
Dean’s afternoons began to include at least one hour of a thorough combing through Castiel's Facebook, looking for any hint of a romantic relationship. The evidence wasn’t too incriminating so far, but he didn’t like the way that Meg Masters person left so many winking faces. After the fourth heart emoticon from some guy named Balthazar (and really, _who the fuck_ names their kid ‘Balthazar’?!) Dean couldn’t take it anymore. He slammed the laptop shut and pushed it away from himself, hitting Sam in the elbow.  
  
“Dean!”  
  
Sam looked up from his homework, looking completely disgusted with his older brother. He slumped down in his chair at the kitchen table and kicked into Dean’s knee, _hard_.  
  
“Shit!” Dean gasped. He would swear later that his voice in no way sounded like a whine. He pushed his chair back abruptly, ready to leap out of it and wrestle his tiny, weakling of a brother to the ground, when a thought crossed his mind. He looked into Sam’s eyes and smiled. When he used this face on female teachers and students, they would practically melt into their shoes and do whatever Dean asked for.  
  
Sam just looked scared.  
  
He was too smart for his own good.  
  
“Sammy, you’re good at hacking, right?”  
  
Sam looked disgusted at this. “No, Dean, I won’t help you _cheat_.”  
  
“I’m not the one cheating, _he_ is!”  
  
“Wait, what?”  
  
Dean’s face flushed bright red when he realized what he had said. He started coughing, and then plowed through the lie. “Cas. He’s cheating on his test. And using Facebook. To cheat. And you know how that could get him kicked out and no scholarship and, well, you know.”  
  
Sam’s eyes stared into Dean’s, hard. He squirmed in his seat. Sammy could be a creepy motherfucker when he wanted to, but, then again, Dean had a general mistrust for kids. You never knew if they were genuinely great or if they were about to pull out knives and try to scalp you. Eventually, Sam sighed and looked back down at his homework.  
  
“I’m not good enough to hack Castiel's Facebook. He’s smart. Unlike-”   
  
The end of Sam’s sentence choked off at the end, the way he did when he knew that whatever he was about to say would earn him a beating from his adoring older brother. Dean immediately made a mental note to himself to change his password. Apparently “bustyasianbeauties69” was not secure enough.  
  
Sam continued him homework in silence for a few moments as Dean scraped his shoe against the leg of his chair.  
  
“I haven’t seen Cas in a month, because he’s babysitting because he said he needs extra money, and he’s missing out on my entire senior year.”  
  
When he looked up, Sam was looking at him as though he was simultaneously the most stupid and most adorable thing Sam had ever seen.  
  
“Dean,” he began in a soft voice. He sounded so much older than his young years when he was quiet. “I’m sure that Cas would spend more time with you if he could. You’re his best friend. But he’s on his own now and he’s in college, so you have to, like...give him space sometimes.”  
  
Dean nodded quietly and stared at his own hands. Sam also sounded older when he was speaking like that. Not for the first time Dean realized that his younger brother was already smarter than Dean would ever be in his entire life.  
  
“You should get a job, too. Holidays and everything.” Sam poked Dean’s hand with the butt of his pencil. “And then you would have less time to stalk Castiel's profile.”  
  
“I’m not stalking,” Dean protested as he reached for the laptop. It was time to send out fifty thousand résumés.  
  
Everything was quiet in the room for a few minutes save for the sound of Dean’s typing and the soft scratching of Sam’s pencil. Dean looked up when he heard the sound of a piece of paper being ripped. He watched Sam fold up a piece of lined notebook paper into an intricate heart-shape, write “open” on one of the tucked flaps, and push it across the table at Dean. He raised his eyes at his little brother, who stared pointedly at him until he opened the paper.  
  
On the paper Sam had written in his too-neat, school-perfect cursive “Do you like-like Cas, check” and two checkboxes below this, one next to the word _yes_ and one next to the word _no._ He had even drawn hearts around the two _like_ s. Dean had seen quite a few of these passed to him before when he was younger, but none of them made his blood pump so loudly in his ears.  
  
Sam knew.  
  
When he looked up, Sam was smiling at him and tapping his pencil against his own chin. Dean couldn’t help but duck his head and smile at the table. He forgot often how young Sam was, apparently young enough for folded, passed notes to be relevant. It was easy to forget when, behind those baby eyes, his brother displayed the most impressive maturity, mature enough to deal with his father’s bullshit, his older brother’s bullshit, and still kick ass in school. Dean could never say any of this out loud, obviously, but he felt like the luckiest fucker in the world to have a kid brother believe in you that much.  
  
Dean placed a very small “x” inside the _Yes_ box and passed it back to Sam, whose smile turned into a full-fledged grin.  
  
“You’re such a girl, Sammy,” he snorted as he opened up Google to search for Christmas gift ideas. Sam deserved the best gift in the fucking world.  
  
\--  
  
One month later and five minutes before the end of Dean’s shift, the phone rang. He groaned (which was still _not_ a whine) and rolled his eyes before picking up the phone. It had already been a long day, he smelled like grease, and he was eager to go home, not make another delivery.  
  
“Roadhouse Pizza, this is Dean speaking, how can I help make your day tastier?” He sped through the speech, hoping that whoever was calling would give up when they couldn’t understand his words, and that maybe he would be able to go home with time to shower and still catch the beginning of Dr. Sexy.  
  
“Dean, this is your chance!”  
  
“Sammy?” Dean’s hand tightened on the phone receiver. “Is everything okay?”  
  
“Yes, Dean, shut up. Kevin Tran just sent me a text that his babysitter tonight is _Cas_ , and if you go take them a pizza now you’ll make it before Kevin’s mom gets back and _just go_.”  
  
Dean squeezed his eyes shut and grinned. Sammy _definitely_ deserved a good Christmas present. He hung up the phone amidst Sam’s high-pitched cheers.  
  
Five minutes, a text from Sam with an address and one freak out later, Dean was running to his Impala, a stolen box (replaced with a note to Ellen to take it out of his paycheck) in tow. He sped out of the parking lot and headed for the lesser-used back roads through town, knowing they were less likely to be used or monitored by police who would _not_ , he was sure, be sympathetic to the love-sick plight of a horny seventeen-year old pizza boy.  
Dean’s heart was already struggling to keep a steady, healthy beat even before he parked on the curb outside the Tran house. By the time he made it up to the Tran’s front door and pressed the button to ring the doorbell, he had all but given up hope on his heart ever physically recovering.  
  
And then Cas opened the door. Dean’s entire body seemed to forget how to function. He almost dropped the pizza and his mouth wobbled into a ridiculous grin.   
  
“Hey, Cas!” he practically shouted this in his friend’s face. For his part, Cas looked equally confused and flustered, and Dean grew scared that he had miscalculated the fuck out of the situation.  
  
“Dean, is that pizza?” Cas cocked his head and eyed the rest of Dean’s body. “Are you a pizza boy now?”  
  
Dean huffed out a laugh and shifted his weight awkwardly. “Yeah, but you would know that if you picked up your phone.”  
  
Before Cas could respond little Kevin Tran poked his head around Castiel's shoulder.  
  
“You’re Sam Winchester’s older brother, right?” Dean’s smile faltered as he nodded at the younger boy. Kevin nodded to himself.   
  
“I thought so. Sam and I are in Pre-Advanced Placement classes together. I suppose we will one day take the SAT together in the same room, because both of our last names begin with a letter toward the end of the alphabet. Is that pizza? I don’t recall ordering pizza. Was this a surprise?”  
  
“Uh, yeah,” Dean said. Absurdly, the only thing he could do after that nerd alert-worthy introduction was hold out the box of pizza. “Do you want it?”  
  
Kevin reached under Castiel's arms, took the pizza, turned around and walked inside the house, presumably to either devour the entire pizza or perform science experiments on it. Dean shrugged a single shoulder at his friend.  
  
“Weird kid.”  
  
“He’ll either be America’s first Asian-American President or he’ll suffer a mental collapse from stress.” The corner of Castiel's mouth twitched. “Come in, Dean.”  
  
Even though he had technically crashed Castiel’s babysitting gig, both Cas and Kevin seemed happy to have Dean around. The three of them tore through the food while watching two episodes of NOVA: Science Now (Kevin’s choice) and one episode of Dr. Sexy (Dean’s choice). Kevin commented on every inaccurate representation of the medical profession, but he also sighed and whispered a girl’s name during a dramatic, declaration-of-love scene. Dean perked his ears up at this.  
  
“Oh? Do you have a girlfriend, Kevin?”  
  
Kevin’s face turned completely red, something which Dean had thought was medically impossible (though he was sure that Kevin could explain to him exactly how it was not just possible but maybe also its rate of occurrence in several different populations).   
  
“Of course not! I’m a nerd.”  
  
Dean snorted at this. “So?”  
  
“So girls don’t _like_ nerds.”  
  
“Bullshit, Kevin. Girls in cartoons don’t like boy nerds in cartoons. In real life, nerds are sexy. Trust me, there is nothing wrong with being smart and making money. That’s one of the things that makes Dr. Sexy so sexy. You have to be a real nerd to be a doctor.”  
  
There was a comfortable silence. A new indie song played on the screen as the sexy urologist and the sexy male nurse made out in the lab. Suddenly, Kevin shot up off of the couch and walked with impressive speed toward the stairs. Cas turned to look after his babysitting charge.  
  
“Are you okay, Kevin?”  
  
“I’m great! I have a girl to talk to! Because I can be sexy!”  
  
Dean whooped with joy and called after the young teenager. “Fuck yeah, Kevin! You can do it!”  
  
Dean moved to turn back around the face the television, but stopped halfway. Cas had turned his body halfway to face Dean, posed with his arm slung over the back of the couch. He stared directly into Dean’s eyes. His stance was predatory, and this did nothing to calm Dean’s nerves. He stared back, frozen, until Cas broke out in laughter. It was infectious; the two of them doubled-over on the couch next to one another, gripping each other’s thighs to keep from falling. When their laughter died down, their heads were tilted back comfortably against the back of the couch facing one another.  
  
“Don’t ever do that to me again, Cas,” Dean whispered. The smile on Castiel's face fell. From this distance, Dean could see every minute movement in Castiel's eyes as they scanned his own.  
  
“What did I do, Dean Winchester?” Dean could feel the small puffs from this whisper.  
  
“Don’t leave me alone, or not respond, or any of that. I know you’re getting older and you’re in college now and you have your own life, and Sammy kept telling me to chill the fuck out, but...” Dean let his sentence trail off. He looked over Castiel's shoulder at the empty pizza box, at Dr. Sexy on the TV. “I don’t know, Cas. I need you, buddy.”  
  
When he looked back it was because of the softest touch of fingers to his jaw. Dean nuzzled into the touch and turned his head slightly into Castiel's hand to place a kiss on his palm. Cas leaned forward and pressed small, soft kisses to the rest of Dean’s face that was exposed and wasn’t being cradled in Castiel's palm. His lips pressed cool and dry to Dean’s cheekbones, trailed to his jaw, and to the side of his mouth. Dean turned very slightly, and then are were kissing, _really_ kissing.  
  
For all of Dean’s teenage, sexual drive, their kisses were surprisingly chaste. He had never been one to romanticize about kissing--because really, what is kissing but the key to unlocking the door to sex?--but this? Now, he was singing a different tune. Kissing Cas was the happiest, most comfortable thing in the world, and even when he opened his mouth and felt Castiel’s tongue explore for the first time it was still the holiest, most pure tongue-kissing that had ever happened, possibly in the history of the world.  
  
Dean was stuck in this rapturous, holy world of Castiel's mouth when the sound of a throat clearing disrupted everything. They sprung apart and looked up, and there was Mrs. Tran.  
  
“Hello, boys,” she cooed. She was barely holding back laughter, her shoulders bobbing and her mouth in a tight smile.  
  
“Kevin is upstairs and he did all of his homework and I’ll completely understand if you won’t re-hire me, but please just know that my homosexuality in no way interferes with my ability to babysit your son.”  
  
Mrs. Tran lost it at this. She reached down and patted Castiel on the cheek.  
  
“I’m not a horrible bitch, Castiel. You’re a smart kid, you are punctual, you are clean, and-” she looked at Dean and winked at him. “-and you have great taste. My son is lucky to have such a good influence watch him, and for so cheap.”  
  
When they left, she pulled Dean back for a moment to threaten him (“he’s a good kid, and I know a lot of people who could hurt you if you hurt him”) and then gave him a short, hard spank as he walked out the door.   
  
It was weird, it was awkward, and it was maybe even illegal in some way. But, more than anything, it was inspiring, especially after Castiel pulled Dean into a hot, needy kiss against the Impala (and really, dreams coming true are _awesome_ ) and asked Dean to come with him back to his dorm.  
  
\--  
  
Dean had barely breathed more than a "let's talk feelings later" before Cas was on him, pressing Dean up against the wall. His hands were immediately under Dean's shirt, moving hot and insistent and pulling a strangled moan from Dean’s throat. For his part, Dean was returning in kind by raking his nails down his friend’s back. He moved his hands down to grab a hold of Castiel's ass and pulled, bringing their erections together. They both gasped aloud at this as their eyes opened wide.   
  
Dean stared into Castiel's eyes and marveled at the fact that only a thin ring of blue remained circling blown pupils. _He_ did that, _Dean_ did that. He reached up and grabbed a hold of Castiel’s face, his palms cupping his friend’s jaw.  
  
“I’m serious. I’ll talk feelings later.”  
  
“Okay,” Cas replied as he rolled his hips forward. Dean’s whole body shook in response to the contact and his eyes fluttered, but he didn’t let go.  
  
“Just please, Cas, know that this isn’t a joke for me.”  
  
Castiel's eyes softened, but there was barely a pause before he was pushing his thigh between Dean’s legs. Dean took advantage of this momentary lack of focus. In one quick motion he maneuvered their bodies to roll them so that Cas was facing the wall and Dean was behind him.  
  
“I’m serious,” he growled into Castiel's ear. To emphasize this he laid a hard smack to Castiel’s ass.  
  
He didn’t expect the low, throaty cry that this would pull out of Castiel. Dean sucked in a breath and stilled his body. He thought briefly about his fantasy from when he first heard of Cas being a babysitter, shuddered, and gave Cas another hard spank. Another loud reaction from Cas (which was sexy as _fuck_ ) had Dean chuckling.  
  
“You’re the babysitter, and I’m the pizza boy,” he murmured into Castiel's ear. His friend groaned, but this time in exasperation.  
  
“You _would_ , Winchester.”  
  
“You trying to get more punishment?” Dean asked playfully. Another smack, another low and shaky moan.  
  
“Your bed.”  
  
It took far too long to get into the bedroom, despite the dorm’s small space. Dean found it impossible to keep his hands off of Cas, now that he had complete permission to touch, feel, and taste. Soon, though, he had Cas bent over the side of his bed with his pants and underwear around his ankles.   
  
“This is so wrong,” Cas moaned into his bed sheets, even as he pushed his hips back and swayed. “This is why I had to stay away from you.”  
  
Dean laughed against Castiel's back. He had Castiel’s shirt rucked up so he could lay hot kisses as he worked down his friend’s back. “I’m barely underage. Give me a few months.”  
  
“Then I’ll have to trade you in for a younger model.”  
  
That earned Cas an immediate spanking.   
  
“Are you doing that on purpose?”  
  
Cas turned his head to look at Dean. The fucker was smirking at him.  
  
“That’s so hot, Cas.”  
  
Cas gave a throaty laugh and pushed his hips back again.  
  
“Then get on with it, Dean.”  
  
Dean moved to his knees so that he was crouched on the ground, his face about level with Castiel's rear. The view was amazing, the pale skin, the surprisingly strong thighs and the heavy and leaking cock that he had a hint of from this angle. Thinking about what his favorite porn actors did, he grabbed at his friend’s ass with both hands and then slapped each cheek in turn, hard smacks from below. Watching the movement and hearing Castiel's muffled moans was making his own cock throb, hard, and reminding him that he was still wearing his jeans. Not even that could distract him, though, not when Cas was literally begging for it. There was a near-constant stream of “that’s good,” “ _fuck_ ” and “I’ve done something wrong, you need to punish me.”   
  
Dean began punctuating the spanking with nips and gentle bites to Castiel’s back and ass.   
  
“Bad boy,” he whispered into his friend’s back. He pulled Castiel’s cheeks--now red and marked--apart just enough to be able to lick a hot stripe. Castiel practically screamed at this and so, taking pity on his friend, Dean reached around and gave Castiel’s erection two firm pumps.  
  
That was all it took before Castiel was coming, bucking his cock back and forth in Dean’s hand and splattering semen against the side of his own bed.  
  
After a second Dean him go. Cas rolled over onto his back. Though he was barely able to move with any coordination, he managed to finally kick his pants off. As Cas watched him, Dean licked and sucked Castiel’s semen off of his fingers and palm. Cas made a noise somewhere between a laugh and a moan.  
  
“I always knew you would be the death of me, Dean.”   
  
Dean smiled and continued to clean his own hand. With his other he pressed his palm against his own penis. Cas noticed this and frowned.  
  
“Let’s switch places.”  
  
“Oh,” Dean whispered. The thought of Castiel touching him and giving him and orgasm was almost enough to make him cum in his own pants. His hips pushed forward into the heel of his hand at this thought. “It’s okay. You don’t need to do anything.”  
  
Cas rolled his eyes and climbed off of his bed. He shucked his shirt off of his body and moved to sit in front of Dean on the ground. He grabbed Dean’s face between his hands and kissed him insistently, his tongue seemingly having decided to taste every corner of Dean’s mouth. Dean moaned helplessly and continued to press against his erection.  
  
Cas moved his hands to hold Dean’s shoulders and gently guided him down until he was laying down on the floor of Castiel’s bedroom. His friend moved quickly to rid Dean of his belt, pants and underwear. Then, he was exposed in front of Cas, who was eyeing his cock with a grin.   
  
“You’re so beautiful, Dean,” he whispered. Then, fulfilling all of Dean’s fantasies and dreams, he took Dean’s cock into his mouth and sucked it, all the way down. Dean barely had enough time to be jealous of whomever had taught Cas to deep-throat, let alone warn Castiel, before his orgasm hit. It was blinding. His back arched, his toes curled, and his entire body shuddered when it hit. Castiel took it without complaint.  
  
Dean couldn’t move, and he was pretty sure he never would again. Castiel had killed him with a crazy fucking orgasm, and he couldn’t be happier.  
  
When he could finally open his eyes, he spotted something shiny under Castiel’s bed. It was a wrapped box.  
  
“What is that?”  
  
Castiel’s eyes went wide. He coughed into his hand and his face’s color began to match the color of his well-loved, well-spanked rear.  
  
“Well, Dean. It might be the other reason why I, you know, needed money and watched kids for money and. Yeah.” He finally lifted his eyes to meet Dean’s. “Happy early Christmas and birthday.”  
  
The whole night had been a fucking roller coaster of emotions for Dean, but nothing could prepare him for this final loop, the rush of adrenaline, the beating of his heart, and the happiness of speeding into something awesome with his best friend. His heart thrummed loudly in his chest as he sat up, leaned forward and kissed Castiel lazily.  
  
“I feel like I’ve already got my present,” he whispered against Castiel’s lips. He had expected this to be received with adoration and maybe for, you know, this to be the time when they could confess their love and make plans for a house and a dog and a litter of happy kids.  
  
Instead, Cas snorted, groaned, and said, “I can’t believe you just said that cheesy line.”  
  
Dean gripped Castiel’s shoulders tight and rolled them back to the ground. He gave Cas another spank, and they kissed between happy, relieved laughs.


End file.
